HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dicyclohexylcarbodiimide → Methyl 6-chloropyridine-3-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dicyclohexylcarbodiimide | HCID 10868 | — |
| Reactant | Phenyl chloroformate | HCID 15891 | — |
| Reactant | Thionyl Chloride | HCID 24386 | — |
| Reactant | 1,1'-Carbonyldiimidazole | HCID 68263 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 6-Chloronicotinic acid | HCID 79222 | — |
| Reactant | N-Hydroxysuccinimide | HCID 80170 | — |
| Reactant | 4-Nitrophenyl chloroformate | HCID 82129 | — |
| Reactant | Carbodiimide | HCID 160435 | — |
| Reactant | Carbonochloridate | HCID 21226386 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | Methyl 6-chloropyridine-3-carboxylate | HCID 254249 | — |
Reaction Steps
6-Chloronicotinic acid 51 is activated by reacting with a chloroformate activating agent such as SOCl2, phenylchloroformate, or p-nitrophenyl chloroformate, or a carbodiimide activating agent such as CDI, DCC, or EDC in the presence of HOBt and N-hydroxysuccinimide in a polar aprotic solvent such as CH2Cl2, 1,2-dichloroethane, DMF, or NMP, and heating. An alcohol such as methanol is then added to form 6-chloronicotinic acid methyl ester 52.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08034950B2 |
| Source dataset | uspto-grants-2011_10 |
| ORD ID | ord-60a83d58b884465ea02acb460b5ea7f2 |
| Source note | uspto-grants-2011_10 |